Hydrochloric Acid → HCID 178440079, compound
Reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:13][CH2:14][CH3:15])[NH:8][C:9]=1[C:10]([OH:12])=[O:11])([CH3:4])[CH3:3].Cl.[CH2:17](O)[CH3:18]>>[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:13][CH2:14][CH3:15])[NH:8][C:9]=1[C:10]([O:12][CH2:17][CH3:18])=[O:11])([CH3:4])[CH3:3]Participants
Conditions
- Temperature
- 35 °C
Procedure
3.0 grams of 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid (formula III) from Example 4, and 30 ml of ethanol were added into 100 ml three-necked flask, anhydrous hydrogen chloride gas was supplied while the temperature was maintained at 30-40° C. until the reaction completed. The reaction mixture was then allowed to cool to ambient temperature, the solvent was evaporated, 30 ml of ethyl acetate and 30 ml of water were added, and the mixture was adjusted to basic using sodium bicarbonate. The organic layer was separated and the aqueous layer was further extracted with 10 ml×3 of ethyl acetate. The organic portion was washed once with saturated saline solution, dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated to give 2.8 grams of ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate, resulting in a yield of 82%.
Workup
- temperatureto cool to ambient temperature
- customthe solvent was evaporated
- addition30 ml of ethyl acetate and 30 ml of water were added
- customThe organic layer was separated
- extractionthe aqueous layer was further extracted with 10 ml×3 of ethyl acetate
- washThe organic portion was washed once with saturated saline solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-db59148a522f4d6fbf2cb80022137c39
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618308B2
Reaction notes
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